Contact and Plantation Periods (1500-1675)

Transportation Routes
Partly because no major river completely transected the Worcester plateau, the important native corridors in this part of central Massachusetts followed overland routes. The primary east-west paths roughly followed today's Long Hill Road to Main Street to Wilder Road. An alternate native route traversed Wataquadoc Hill via Old Bay Road. A north-south route through Bolton followed the Still River, probably along the line of Still River Road or slightly to its west.
Early travel by English trappers and traders utilized the native trails. Travel through the Bolton area was more frequent after 1636, when there was increased overland movement between Massachusetts Bay and the settlements of the Connecticut River valley. In 1648 the northern alternate to the earlier Boston to Springfield route was in use through the Lancaster territory as the third major colonial roadway of the Plantation Period, involving both the Old Bay and Main Street sections of what had come to be known as the "Bay Path." A short time later, in 1656, the Massachusetts Bay Colony laid out the Concord/Lancaster Road along the existing north branch of the Bay Path that traversed the north side of Wataquadoc Hill.
The earliest route laid out by the Lancaster proprietors through Bolton was probably the way north to the "plumtrees and Groten" that followed the east side of the Nashua River. It was later relocated a short distance to the east to higher ground along the general line of Still River Road/Route 110, where it was officially laid out in 1674.
Settlement Pattern and Population
The territory now encompassed by Bolton was located just east of the Nashua River from some permanent camps of the Nashua (Nashaway) group of Nipmucks located in Lancaster and Sterling, and it is therefore unlikely that there were any substantial camps within Bolton's present borders. Early native fishing sites within Bolton are likely to have been located at the ponds, and it is most likely that any camps associated with fishing, hunting, or gathering, were small, and of short duration.
During the seventeenth century, epidemics decimated the Indian population, and regional tribal wars killed many of their people. In 1643, the regional tribal leader, Sachem Solan, sold what was later established by the General Court as the 10- by 8-mile Nashaway Plantation grant to the English, and most of the remaining Nashaways withdrew to the west.
The Nashaway Plantation represents the first land granted by the General Court in the central Massachusetts region. With the same boundaries, it was incorporated as the town of Lancaster in 1653. The first English settlers made their homes in the clustered village at Lancaster "old common". Gradually, the outlying parts of the town, which included the territory of Bolton, were divided into privately-owned parcels in the second (1659), third, and later divisions of Lancaster lands, but only a few hardy farmers built houses on them. There are references to a road by Abraham Joslin's house on the west side of Long Hill in 1670, for instance, and to Ens. John Moore's house east of Wataquadoc by 1665. Some English farmers certainly utilized meadows and pastures in Bolton, and would have entered the territory for hunting, mowing, and other transient activities.
In general, however, the region as a whole attracted only a small number of settlers during the period, with Lancaster holding only fifty families by 1676. Then, after a period of increasing unrest between the settlers and the Indians, King Philip's War broke out in 1675. The English village at the center of Lancaster was destroyed, and settlers there were massacred or captured. The colonists abandoned the town entirely for several years.